Cinnoline, 4-methyl- → 2-(1-aminopropan-2-yl)aniline

HRID 380181Notes

Reaction equation

HRID 380181 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1>CO.[Ni]>[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH:2]([CH3:1])[CH2:3][NH2:4]

Participants

4

Reactant 1

HCID 26843Cinnoline, 4-methyl-

Product 1

HCID 4135152-(1-aminopropan-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Reduction of 4-methyl-cinnoline (10 g, 69.5 mmol) in methanol (100 mL), using Raney nickel (3 g). The catalyst was removed and washed with methanol. The filtrate was treated with an excess of HCl in isopropanol; ether was then added and the solution cooled. The precipitate was filtered and dried; 9.4 g (60%).

Workup

  1. customThe catalyst was removed
  2. washwashed with methanol
  3. additionThe filtrate was treated with an excess of HCl in isopropanol
  4. additionether was then added
  5. temperaturethe solution cooled
  6. filtrationThe precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-f5ea5606d1254eb3a8970a90b37e595f
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

Loading…